(16R,20R,21Ξ)-7β,9,20-trihydroxy-21-methoxy-16-methyl-1-oxo-10-phenyl-9,23-seco-[13]cytochalasa-6(12),13t-dien-23-oic acid 20-lactone | 59861-37-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (16R,20R,21Ξ)-7β,9,20-trihydroxy-21-methoxy-16-methyl-1-oxo-10-phenyl-9,23-seco-[13]cytochalasa-6(12),13t-dien-23-oic acid 20-lactone
• 英文别名: (21Ξ)-21-methoxy-21,22-dihydro-cytochalasin-B acid 20-lactone
• CAS: 59861-37-9
• 化学式: C₃₀H₄₁NO₆
• 分子量: 511.659
• InChiKey: XVZWVVXPCPYIPG-ADGCGQRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  37.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  105.09
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  细胞松弛素B 、 甲醇 在 sodium hydroxide 作用下， 生成 (16R,20R,21Ξ)-7β,9,20-trihydroxy-21-methoxy-16-methyl-1-oxo-10-phenyl-9,23-seco-[13]cytochalasa-6(12),13t-dien-23-oic acid 20-lactone
  参考文献：
  名称：

  Cytochalasin B (Phomin): Abbaureaktionen und Cyclisierung der B-Cytochalasinsäure zu 21,22-Dihydro-isocytochalasin A

  摘要：

  Cytochalasin B (Phomin): Degradation Reactions and Cyclization of B‐Cytochalasinic Acid to 21,22‐Dihydro‐Isocytochalasin ATreatment of the γ‐lacton 5, a transformation product of cytochalasin B (phomin) (1), with OsO4 gave the dihydroxy derivatives 6 and 7. Cleavage of the former by NaIO4 in aqueous methanol yielded a mixture of the dimethylacetal 10 and the unsaturated aldehyde 11, which are potential intermediates for a total synthesis of cytochalasins. Cytochalasin B (1) was hydrolysed with NaOH in aqueous dioxane to B‐cytochalasinic acid (14). Recyclization of 14 using the Mukaiyama‐Corey method [19] [20] did not yield cytochalasin B (1) but the isomeric 21,22‐dihydro‐isocytochalasin A (18). Treatment of 14 according to Gerlach [21] yielded the phthalimidine 19.

  DOI：

  10.1002/hlca.19760590322